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Encyclopedia > Organophosphorus

Organophosphorus compounds are chemical compounds containing carbon-phosphorus bonds. Organophosphorus chemistry is the corresponding science exploring the properties and reactivity of organophosphorus compounds. Phosphorus shares group 15 in the periodic table with nitrogen and phosphorus compounds and nitrogen compounds have much in common.[1][2] Look up chemical compound in Wiktionary, the free dictionary. ... For other uses, see Carbon (disambiguation). ... General Name, symbol, number phosphorus, P, 15 Chemical series nonmetals Group, period, block 15, 3, p Appearance waxy white/ red/ black/ colorless Standard atomic weight 30. ... A chemical bond is the physical process responsible for the attractive interactions between atoms and molecules, and that which confers stability to diatomic and polyatomic chemical compounds. ... Nitrogen is the 7th element in the Periodic Table. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ...


Phosphorus can adopt oxidation states −3, −1, 1, 3 and 5. In chemical literature very often compounds with +3 or −3 oxidation state are grouped together as having a (III) oxidation state regardless of sign. In an official and more descriptive nomenclature phosphorus compounds are identified by their coordination number δ and their valency λ. In this system a phosphine is a δ3λ3 compound. In chemistry, the oxidation state is an indicator of the degree of oxidation of an atom in a chemical compound. ... In chemistry coordination number (c. ... For other uses, see Sigma (disambiguation). ... In chemistry, valence, also known as valency or valency number, is a measure of the number of chemical bonds formed by the atoms of a given element. ... Look up Λ, λ in Wiktionary, the free dictionary. ...

Contents

Phosphanes & phosphines

The parent compound of the phosphanes is PH3, called phosphine in the US and UK and phosphane elsewhere.[3] Replacement of one or more protons by an organic residue, gives PH3−xRx, an organophosphine or organophosphane, again depending on the country. The phosphorus atom in phosphanes/phosphines has a formal oxidation state −3 (δ3λ3) and are the phosphorus analogues of simple amines. The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ...


An often used organic phosphine is triphenylphosphine. Like amines, phosphines have a trigonal pyramidal molecular geometry although with larger angles. The C-P-C bond angle is 98.6° for trimethylphosphine increasing to 109.7° when the methyl groups are replaced by tert-butyl groups. Commonly the size of these ligands are described by the parameter called cone angle. Triphenylphosphine (in Europe: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 - often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. ... In chemistry, a trigonal pyramid is a molecular geometry with one atom at the apex and three atoms at the corners of a trigonal base. ... Geometry of the water molecule Molecules have fixed equilibrium geometries--bond lengths and angles--that are dictated by the laws of quantum mechanics. ... In organic chemistry, butyl is a four-carbon alkyl substituent with chemical formula -C4H9. ... Ligand cone angle is a measure of the size of a ligand. ...


The barrier to inversion is also much higher than in amines for a process like nitrogen inversion to occur and therefore phosphines with three different substituents can display optical isomerism. In chemistry, a nitrogen compound like ammonia in a trigonal pyramid geometry undergoes rapid nitrogen inversion whereby the molecule turns inside out. ... In organic chemistry, a substituent is an atom or group of atoms substituted in place of a hydrogen atom on the parent chain of a hydrocarbon. ... Optical isomerism is a form of isomerism (specifically stereoisomerism) where the two different isomers are the same in every way except being non-superposable mirror images of each other. ...


The basicity of phospines is less than that of corresponding amines, for instance phosphonium ion itself has a pKa of -14 compared to 9.21 for ammonium ion; trimethylphosphonium has a pKa of 8.65 compared to that of 9.76 of trimethylamine; and triphenylphosphonium (pKa 11.2) is less basic than triphenylammonium (pKa 19). In chemistry and biochemistry, acid dissociation constant, the acidity constant, or the acid-ionization constant () is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... In chemistry and biochemistry, acid dissociation constant, the acidity constant, or the acid-ionization constant () is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... Trimethylamine, also known as NMe3, N(CH3)3, and TMA, is a colorless, hygroscopic, and flammable simple amine with a typical fishy odor in low concentrations and an ammonia-like odor in higher concentrations. ...


Amines and phosphines both have a lone pair of electrons but with a difference. Whereas the lone pair in an amine shares its electrons at every opportunity for delocalization for instance in pyridine, the phosphorus atom in a similar configuration will not. For this reason, the phosphorus equivalent of pyrrole called phosphole is not at all aromatic. A lone pair is an electron pair without bonding or sharing with other atoms. ... In chemistry, delocalized electrons are electrons in a molecule that do not belong to a single atom or a covalent bond. ... Pyridine is a chemical compound with the formula C5H5N. It is a liquid with a distinctively putrid odour. ... Pyrrole, or pyrrol, is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H5N. Pyrroles are components of larger aromatic rings, including the porphyrins of heme, the chlorins and bacteriochlorins of chlorophyll, and the corrin ring of vitamin B12. ... Phosphole is an organic compound with the chemical formula C4H5P; it is the the phosphorus analog of pyrrole. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ...


The reactivity of phosphines match that of amines with regard to nucleophilicity in the formation of Phosphonium salts with the general structure PR4+X. This property is used in the Appel reaction converting alcohols to alkyl halides. In chemistry, a nucleophile (literally nucleus lover) is a reagent which is attracted to centres of positive charge. ... A phosphonium salt is a salt containing the phosphonium (PH4+) ion such as phosphonium iodide (PH4+I−). It may also refer to an organic derivative such as tetramethylphosphonium iodide, [P(CH3)4]+I−. Alkyltriphenylphosphonium salts are widely used for the preparation of Wittig reagents for the Wittig reaction. ... The Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride . ... This article does not cite any references or sources. ... In chemistry, an alkyl halide is an organic molecule of the form R_X, where X is a halide and R contains a carbon atom bonded to other functional groups or hydrogens. ...


A difference in reactivity with amines is the ease of oxidation of phosphines to phosphine oxides. The most fundamental reactions in chemistry are the redox processes. ...


Synthesis

Synthetic produces for phosphines are:

In chemistry, nucleophilic substitution is a class of substitution reaction in which an electron-rich nucleophile attacks a molecule and replaces a group or atom, called the leaving group. ... A Grignard Reagent is an alkyl- or aryl- magnesium halide. ... Sodium amide, also called sodamide, is NaNH2. ... In chemistry, an alkyl halide is an organic molecule of the form R_X, where X is a halide and R contains a carbon atom bonded to other functional groups or hydrogens. ... In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is removed by the creation of two new covalent bonds by the addition of a nucleophile. ... This article is about the chemical compound. ... The chemical compound potassium hydroxide, (KOH) sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base. ... Dimethyl sulfoxide (DMSO) is the chemical compound with the formula (CH3)2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. ... In chemistry, Markovnikovs rule is an observation based on Zaitsevs rule. ... General Name, Symbol, Number phosphorus, P, 15 Chemical series nonmetals Group, Period, Block 15, 3, p Appearance waxy white/ red/ black/ colorless Atomic mass 30. ... The chemical compound potassium hydroxide, (KOH) sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base. ... Acrylonitrile (CH2=CH-C≡N), is a pungent smelling, extremely flammable organic liquid. ... Image File history File links Phosphineadditionsalkenes. ... In Organic chemistry, a radical addition reaction is an addition reaction in which the first species that adds is a radical. ... Azobisisobutyronitrile, also azobisisobutylonitrile, is a toxic white crystalline compound often used as a foamer in plastics and rubber. ... A peroxide is a compound containing an oxygen-oxygen single bond. ... In organic chemistry, a nucleophilic addition reaction is an addition reaction where in a chemical compound a pi bond is removed by the creation of two new covalent bonds by the addition of a nucleophile. ... The structural formula of 2-butyne, a simple alkyne-containing molecule Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. ... Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. ... Chlorosilanes are a group of reactive, chlorine-containing chemical compounds, related to silane and used in many chemical processes. ...

Reactions

The main reaction types of phosphines are:

  • as nucleophiles for instance with alkyl halides to phosphonium salts. Phospines are key nucleophilic catalysts in the dimerization of enones in the Rauhut-Currier reaction.
  • as reducing agents:
Phosphines are reducing agents in the Staudinger reduction converting azides to amines and in the Mitsunobu reaction converting alcohols into esters. In these processes the phosphine is oxidized to the phosphine oxide. Phosphines have also been found to reduce activated carbonyl groups for instance the reduction of an α-keto ester to an α-hydroxy ester in scheme 2.[5] In the proposed reaction mechanism the first proton is on loan from the methyl group in trimethylphosphine (triphenylphosphine does not react).
When modified with suitable substituents as in certain diazaphospholenes (scheme 3) the polarity of the P-H bond can actually be inverted (see: umpolung) and the resulting phosphine hydride can reduce a carbonyl group as in the example of benzophenone in yet another way.[6]
  • Multidentate phosphines such as BINAP are important ligands in organometallic chemistry.

In chemistry, an alkyl halide is an organic molecule of the form R_X, where X is a halide and R contains a carbon atom bonded to other functional groups or hydrogens. ... A phosphonium salt is a salt containing the phosphonium (PH4+) ion such as phosphonium iodide (PH4+I−). It may also refer to an organic derivative such as tetramethylphosphonium iodide, [P(CH3)4]+I−. Alkyltriphenylphosphonium salts are widely used for the preparation of Wittig reagents for the Wittig reaction. ... The Rauhut-Currier reaction is an organic reaction describing the dimerization or isomerization of enones by action of an organophosphine of the type R3P.[1] The reaction mechanism is essentially that of the related and better known Baylis-Hillman reaction (DABCO not phosphine, carbonyl not enone) but the Rauhut-Currier... A reducing agent (also called a reductant or reducer) is the element or a compound in a redox (reduction-oxidation) reaction (see electrochemistry) that reduces another species. ... The Staudinger ligation or Staudinger reaction or Staudinger reduction is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces a phosphorimidate . Combined with the hydrolysis of the phosphorimidate, to produce a phosphine oxide and an amine, this reaction is a mild method of... The Mitsunobu reaction is an organic reaction that can convert an alcohol into a variety of functional groups, such as esters using triphenylphosphine and diethyl azodicarboxylate (DEAD). ... In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs. ... Image File history File links Phosphine_ester_reduction. ... Umpolung or polarity inversion in organic chemistry is the chemical modification of a functional group with the aim the reversal of polarity of that group. ... Hydride is the name given to the negative ion of hydrogen, H−. Although this ion does not exist except in extraordinary conditions, the term hydride is widely applied to describe compounds of hydrogen with other elements, particularly those of groups 1–16. ... Benzophenone, also known as diphenylmethanone, phenyl ketone, diphenyl ketone, or benzoylbenzene. ... Image File history File links Phosphine_umpolung. ... (S)- and (R)-BINAP Ball and stick model of BINAP viewed as above In organic chemistry, BINAP, an acronym used for 2,2-bis(diphenylphosphino)-1,1-binaphthyl, is an important chiral ligand widely used in asymmetric synthesis. ... In chemistry, a ligand is an atom, ion, or molecule (see also: functional group) that generally donates one or more of its electrons through a coordinate covalent bond to, or shares its electrons through a covalent bond with, one or more central atoms or ions (these ligands act as a...

Phosphanes

Primary phosphanes are under-used in chemistry due to their general lack of stability towards oxygen. One study[7] reports on several novel air-stable aromatic primary phosphanes prepared by organic reduction of the corresponding phosphonate: Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. ... Phosphonates or Phosphonic acids are organic compounds containing one or more C-PO(OH)2 groups. ...

The stability is attributed to conjugation between the aromatic ring and the phosphorus lone pair. Image File history File links Size of this preview: 800 × 260 pixelsFull resolution‎ (981 × 319 pixels, file size: 8 KB, MIME type: image/png) Phosphane Stability I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU... A chemically conjugated system, is a system of atoms covalently bonded with alternating single and double bonds (e. ... Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. ... A lone pair is an electron pair without bonding or sharing with other atoms. ...


Phosphine oxides

Phosphine oxides (designation δ3λ3) have the general structure R3P=O with formal oxidation state −1. Phospines form hydrogen bonds and many phosphines are therefore soluble in water. The P=O bond is very polar with a dipole moment of 4.51 D for triphenylphosphine. An example of a quadruple hydrogen bond between a self-assembled dimer complex reported by Meijer and coworkers. ... Dipole moment refers to the quality of a system to behave like a dipole. ...


The nature of the phosphorus to oxygen double bond is a matter of debate. Pentavalent phosphorus like nitrogen is not compatible with the octet rule. In older literature the bond is represented as a dative bond just like an amine oxide. The prevailing view is that of a full double bond with back bonding taking place between a filled oxygen electron pair and an empty phosphorus d-orbital (lacking in nitrogen). problem is: the P=O bond does not react as any C=C double bond as addition reactions are absent and involvement of a phosphorus d-orbital in bonding is not supported in silico. Alternative theories favor an ionic bond P+−O which on its own strength should explain the short bond length. Molecular Orbital Theory proposes that the short bond length is attributed to the donation of the lone pair electrons from oxygen to the antibonding phosphorus-carbon bonds. This proposal is supported by ab initio calculations and has gained consensus in the chemistry community. The bonding in carbon dioxide The octet rule is a simple chemical rule of thumb that states that atoms tend to combine in such a way that they each have eight electrons in their valence shells, similar to the electronic configuration of a noble gas. ... A coordinate covalent bond (also known as dative covalent bond) is a special type of covalent bond in which the shared electrons come from one of the atoms only. ... An amine oxide, also known as amine-N-oxide and N-oxide, is a chemical compound that contains the functional group R3N+-O− (sometimes written as R3N=O or R3N→O). ... Ï€ backbonding, also called Ï€ backdonation, is a concept from chemistry, that refers to the flow of electrons from an atomic orbital on one atom to a Ï€ anti-bonding orbital that belongs to other atoms. ... An addition reaction, in chemistry, is in its simplest terms an organic reaction where two or more molecules combine to form a larger one. ... In Silico is a full length artist album by Deepsky View From a Stairway Jareths Church The Mansion World (Deepskys Trippin In Unknown Territory Mix) Ride Three Sheets to the Wind Atia Metro Smile Cosmic Dancer (2002 remix) Until the End of the World Let Me Live Categories... Sodium and chlorine bonding ionically to form sodium chloride. ... In molecular geometry, bond length or bond distance is the distance between two bonded atoms in a molecule. ... In chemistry, molecular orbital theory (MO theory) is a method for determining molecular structure in which electrons are not assigned to individual bonds between atoms, but are treated as moving under the influence of the nuclei in the whole molecule. ...


Phospines are easily oxidized to phosphine oxides as examplified by the directed synthesis of a phospha crown, the phosphorus analogue of an aza crown[8] where it is not possible to isolate the phosphine itself.[9] Cyclen or 1,4,7,10-tetraazacyclododecane is a macrocycle and the aza analogue of crown ethers. ...

Image File history File links Download high resolution version (1011x685, 19 KB) Summary Phosphacrowns Licensing I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU Free Documentation License, Version 1. ...

Phosphonates

Phosphonates have the general structure R−P(=O)(OR)2. In the Horner-Wadsworth-Emmons reaction and the Seyferth-Gilbert homologation phosphonates are used as stabilized carbanions in reactions with carbonyl compounds. Phosphonates have many technical applications and bisphosphonates are a class of drugs. Phosphonates or Phosphonic acids are organic compounds containing one or more C-PO(OH)2 groups. ... The Horner-Wadsworth-Emmons reaction is the chemical reaction of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes. ... The Seyferth-Gilbert homologation is a the chemical reaction of an aryl ketone 1 (or aldehyde) with dimethyl (diazomethyl)phosphonate 2 and potassium tert-butoxide to give substituted alkynes 3. ... A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom : C=O. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex (a metal carbonyl, e. ... In pharmacology, bisphosphonates (also called: diphosphonates) is a class of drugs that inhibits the resorption of bone. ...


Phosphite and phosphate esters

Phosphite esters or phosphites have the general structure P(OR)3 with oxidation state +3. Phosphites are employed in the Perkow reaction and the Arbusov reaction. Phosphate esters with the general structure P(=O)(OR)3 and oxidation state +5 are of great technological importance as flame retardant agents and plasticizers. Lacking a P−C bond, these compounds are technically not organophosphorus compounds. We dont have an article called Phosphite ester Start this article Search for Phosphite ester in. ... The Perkow reaction is an organic reaction in which a trialkyl phosphite ester reacts with a haloketone to form a vinyl phosphonate and an alkyl halide. ... The Michaelis-Arbuzov reaction is the chemical reaction of a trialkyl phosphite and an alkyl halide to form a phosphonate. ... An organophosphate (sometimes abbreviated OP) is the general name for esters of phosphoric acid and is one of the organophosphorus compounds. ... Socks made from flame retardant cotton. ... Plasticizers are additives that soften the materials (usually a plastic or a concrete mix) they are added to. ...


Phosphoranes

Phosphoranes have a −5 oxidation state (δ5λ5) with parent compound the non-stable phosphoran PH5 or λ5-phosphane (lambda 5 phosphane). Phosphorus ylides are unsaturated phosphoranes used in the Wittig reaction. A phosphorane is a functional group in chemistry with pentavalent phosphorus. ... An ylide is a neutral molecule with positive and negative charges on adjacent atoms. ... The Wittig reaction is a chemical reaction of an aldehyde or ketone with a phosphonium ylide to give an alkene and triphenylphosphine oxide. ...


Phosphorus multiple bonds

Many compounds exist with carbon phosphorus multiple bonds (P=C) as phosphaalkenes (R2C::PR) and phosphaalkynes (RC:::PR). In the compound phosphorine one carbon atom in benzene is replaced by phosphorus. The reactivity of phosphaalkenes is often compared to that of alkenes and not to that of imines. The reason is that the HOMO of phosphaalkenes is not the phosphorus lone pair (as in imines the amine lone pair) but the double bond. Therefore like alkenes, phosphaalkenes engage in Wittig reactions, Peterson reactions, Cope rearrangements and Diels-Alder reactions. In chemistry, phosphaalkyne is a molecule which has a phosphorus-carbon triple bond. ... Chemical structure of phosphorine Phosphorine is a heavy benzene containing a phosphorus atom instead of a CH moiety, so it is considered to be a heavier element analog of pyridine. ... This article is about the chemical compound. ... The general structure of an imine An imine is a functional group or chemical compound containing a carbon-nitrogen double bond. ... Look up homo, homo- in Wiktionary, the free dictionary. ... A lone pair is an electron pair without bonding or sharing with other atoms. ... The Wittig reaction is a chemical reaction of an aldehyde or ketone with a phosphonium ylide to give an alkene and triphenylphosphine oxide. ... The Peterson olefination (also called the Peterson reaction) is the chemical reaction of α-silyl carbanions 1 with ketones (or aldehydes) to form a β-hydroxysilane 2 which eliminates to form alkenes 3. ... It has been suggested that Cope reaction be merged into this article or section. ... The Diels-Alder reaction The Diels-Alder reaction is an organic chemical reaction (specifically, a cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. ...


The first phosphaalkene was synthesised in 1974 by Becker as a keto-enol tautomerism akin a Brook rearrangement: In organic chemistry, keto-enol tautomerism refers to a chemical equilibrium between a keto form (a ketone or an aldehyde) 1 and an enol 2. ... The Brook rearrangement in organic chemistry is a rearrangement reaction in which a organosilyl group switches position with a hydroxyl proton over a carbon to oxygen covalent bond under the influence of a base . ...

with R = methyl or phenyl and tms representing trimethylsilyl. Image File history File links No higher resolution available. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 Picture where the six carbon atoms are arranged in a cyclic manner. ... Chemical structure of a Trimethylsilyl group A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. ...


In the same year Harold Kroto established spectroscopically that thermolysis of Me2PH yielded CH2=PMe. Harold Kroto Sir Harold Walter Kroto, FRS (born 7 October 1939) is an English chemist and one of the winners of the 1996 Nobel Prize in Chemistry. ... Thermolysis (from thermo- meaning heat and -lysis meaning break down) is a chemical process by which a substance is decomposed into other substances by use of heat. ...


A general method for the synthesis of phosphaalkenes is by 1,2-elimination of suitable precursors, initiated thermally or by base such as DBU, DABCO or triethylamine: An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one or two-step mechanism. ... DBU or 1,8-diazabicyclo(5. ... DABCO or 1,4-diazabicyclo[2. ... Triethylamine, also known as N,N-diethylethanamine, TEN or N,N,N-Triethylamine, is a colorless, volatile liquid with a strong, unpleasant and fishy smell reminiscent of ammonia. ...

The Becker method is used in the synthesis of the phosphorus pendant of Poly(p-phenylene vinylene):[10] Image File history File links Size of this preview: 800 × 129 pixelsFull resolution‎ (858 × 138 pixels, file size: 3 KB, MIME type: image/png) Phosphaalkene General I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of the GNU... Poly(p-phenylene vinylene) (PPV) is conducting polymer of the rigid-rod polymer host family. ...

Diphosphenes are compounds containing P=P phosphorus double bonds. Phosphazenes have a P=N double bond. Image File history File links Size of this preview: 800 × 383 pixelsFull resolution‎ (1,030 × 493 pixels, file size: 10 KB, MIME type: image/png) Poly(p-phenylenephosphaalkene) I, the creator of this work, hereby grant the permission to copy, distribute and/or modify this document under the terms of... In chemistry, diphosphene is a molecule that has a phosphorus-phosphorus double bond, indicated by R-P=P-R. Diphosphenes are heavier analogues of azo compounds. ... A phosphazene is any of a class of chemical compounds in which a phosphorus atom is covalently linked to a nitrogen atom by a double bond and to three other atoms or radicals by single bonds. ...


See also

CH He
CLi CBe CB CC CN CO CF Ne
CNa CMg CAl CSi CP CS CCl Ar
CK CCa CSc CTi CV CCr CMn CFe CCo CNi CCu CZn CGa CGe CAs CSe CBr Kr
CRb CSr CY CZr CNb CMo CTc CRu CRh CPd CAg CCd CIn CSn CSb CTe CI Xe
CCs CBa CHf CTa CW CRe COs CIr CPt CAu CHg CTl CPb CBi CPo CAt Rn
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Uub Uut Uuq Uup Uuh Uus Uuo
La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
Ac Th Pa CU Np Pu Am Cm Bk Cf Es Fm Md No Lr
Chemical bonds to carbon
Core organic chemistry many uses in chemistry.
Academic research, but no widespread use Bond unknown / not assessed.

This article is about the chemical. ... Phosphine oxide, organophosphorus compounds with the fromula - OPR3 Phosphine - PR3 Phosphinite - P(OR)R2 Phosphonite - P(OR)2R Phosphite - P(OR)3 Phosphinate - OP(OR)R2 Phosphonate - OP(OR)2R Phosphate - OP(OR)3 ... Phosphinite, an organophosphorus compounds with the fromula P(OR)R2 Phosphine - PR3 Phosphine oxide - OPR3 Phosphonite - P(OR)2R Phosphite - P(OR)3 Phosphinate - OP(OR)R2 Phosphonate - OP(OR)2R Phosphate - OP(OR)3 ... Phosphonite, organophosphorus compounds with the fromula P(OR)2R Phosphine - PR3 Phosphine oxide - OPR3 Phosphinite - P(OR)R2 Phosphite - P(OR)3 Phosphinate - OP(OR)R2 Phosphonate - OP(OR)2R Phosphate - OP(OR)3 ... The phosphite ion is a polyatomic ion with phosphorus as its central atom. ... Phosphinate, organophosphorus compounds with the fromula OP(OR)R2 Phosphine - PR3 Phosphine oxide - OPR3 Phosphinite - P(OR)R2 Phosphonite - P(OR)2R Phosphite - P(OR)3 Phosphonate - OP(OR)2R Phosphate - OP(OR)3 ... Phosphonates or Phosphonic acids are organic compounds containing one or more C-PO(OH)2 groups. ... A phosphate, in inorganic chemistry, is a salt of phosphoric acid. ... Chemical structure of methane, the simplest alkane Alkanes, also known as Paraffins, are chemical compounds that consist only of the elements carbon (C) and hydrogen (H) (i. ... An organolithium reagent is an organometallic compound with a direct bond between a carbon and a lithium atom. ... The organometallic chemistry of group 2 elements is relevant to organic chemistry, though in some cases, the interest is strictly academic. ... Organoborane or organoboron compounds are chemical compounds comprised of boron and carbon. ... A carbon-carbon bond is a covalent bond between two carbon atoms. ... A carbon-nitrogen bond is a covalent bond between carbon and nitrogen and one of the most abundant in organic chemistry and biochemistry [1]. Nitrogen has five valence electrons and in simple amines it is trivalent with two remaining electrons forming a lone pair. ... A carbon-oxygen bond is a covalent bond between carbon and oxygen and one of the most abundant in organic chemistry and biochemistry [1]. Oxygen has 6 valence electrons and prefers to share two electrons in bonding with carbon, leaving the remaining 4 nonbonding in 2 lone pairs. ... Some important fluorocarbons. ... The organometallic chemistry of group 2 elements is relevant to organic chemistry, though in some cases, the interest is strictly academic. ... An organoaluminium compound is an organometallic compound with a carbon to aluminium bond. ... Organosilicon compounds are chemical compounds containing carbon silicon bonds. ... Organosulfur compounds are organic compounds that contain sulfur. ... An organochloride, organochlorine or chlorocarbon, is an organic compound containing at least one covalently bonded chlorine atom. ... The organometallic chemistry of group 2 elements is relevant to organic chemistry, though in some cases, the interest is strictly academic. ... Organotitanium compounds in organometallic chemistry contain carbon to titanium chemical bonds. ... Organonickel chemistry is a branch of organometallic chemistry that deals with organic compounds containing a nickel to carbon bond and their reactions [1] [2]. They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. ... Organocopper compounds in organometallic chemistry contain carbon to copper chemical bonds. ... Organozinc compounds in organic chemistry contain carbon to zinc chemical bonds. ... Organogermanium compounds are organometallic compounds containing a carbon to germanium or hydrogen to germanium chemical bond. ... An organoarsenic compound in organic chemistry is an organic compound containing a chemical bond between arsenic and carbon. ... Organoselenium compounds are chemical compounds containing carbon to selenium bonds. ... Halocarbon compounds are chemicals in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms: fluorine, chlorine, bromine or iodine. ... A zirconocene Kaminsky catalyst for producing syndiotactic polypropylene Organozirconium compounds are organometallic compounds containing a carbon to zirconium chemical bond. ... Organopalladium chemistry is a branch of organometallic chemistry and deals with organic palladium compounds and their reactions. ... An organocadmium compound is a organometallic compound containing a carbon to cadmium chemical bond. ... Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. ... Halocarbon compounds are chemicals in which one or more carbon atoms are linked by covalent bonds with one or more halogen atoms: fluorine, chlorine, bromine or iodine. ... Organomercury refers to the group of organometallic compounds containing mercury. ... Organolead compounds are chemical compounds containing a chemical bond between carbon and lead. ... Organouranium compounds are organometallic compounds containing a carbon to uranium chemical bond. ... A chemical bond is the physical process responsible for the attractive interactions between atoms and molecules, and that which confers stability to diatomic and polyatomic chemical compounds. ... For other uses, see Carbon (disambiguation). ...

External links

  • organophosphorus chemistry @ http://users.ox.ac.uk Link
  • NMR predictor for organophosphorus compound chemical shifts from Alan Brisdon's Research Group

Link


References

  1. ^ Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus. The Carbon Copy; John Wiley & Sons, 1997. ISBN 0-471-97360-2
  2. ^ Quin, L. D. A Guide to Organophosphorus Chemistry; John Wiley & Sons, 2000. ISBN 0-471-31824-8
  3. ^ Gold Book: Link
  4. ^ Arbuzova, S. N.; Gusarova, N. K.; Trofimov, B. A. "Nucleophilic and free-radical additions of phosphines and phosphine chalcogenides to alkenes and alkynes." Arkivoc 2006, part v, 12–36 (EL-1761AR). Article
  5. ^ Zhang, W.; Shi, M. "Reduction of activated carbonyl groups by alkyl phosphines: formation of α-hydroxy esters and ketones." Chem. Commun. 2006, 1218–1220. doi:10.1039/b516467b
  6. ^ Burck, S.; Gudat, D.; Nieger, M.; Du Mont, W.-W. "P-Hydrogen-Substituted 1,3,2-Diazaphospholenes: Molecular Hydrides." J. Am. Chem. Soc. 2006, 128, 3946–3955. doi:10.1021/ja057827j
  7. ^ Taming a Functional Group: Creating Air-Stable, Chiral Primary Phosphanes Rachel M. Hiney, Lee J. Higham, Helge Müller-Bunz, Declan G. Gilheany Angewandte Chemie International Edition Volume 45, Issue 43 , Pages 7248 - 7251 2006 doi:10.1002/anie.200602143
  8. ^ Edwards, P. G.; Haigh, R.; Li, D.; Newman, P. D. "Template Synthesis of 1,4,7-Triphosphacyclononanes." J. Am. Chem. Soc. 2006, 128, 3818–3830. doi:10.1021/ja0578956
  9. ^ In step 1 diphosphinoethane coordinates to a ferrocene containing additional carbon monoxide ligands and an acetonitrile ligand. The next step is a hydrophosphination with trivinylphosphine followed by alkylation with ethyl bromide and hydrogenation with hydrogen over palladium on carbon. In the final step the iron template is removed by bromine but oxidation of the phosphine groups is unavoidable
  10. ^ Phosphorus Copies of PPV: -Conjugated Polymers and Molecules Composed of Alternating Phenylene and Phosphaalkene Moieties Vincent A. Wright, Brian O. Patrick, Celine Schneider, and Derek P. Gates J. Am. Chem. Soc.; 2006; 128(27) pp 8836 - 8844; (Article) doi:10.1021/ja060816l

  Results from FactBites:
 
Organophosphorus pesticides (PIM G001) (9245 words)
Organophosphorus pesticides are used to control insect vectors which are found in food and commercial crops, and infestations in domestic and commercial buildings, and in man or domestic animals.
Organophosphorus pesticides exert their acute effects by inhibiting acetylcholinesterase in the nervous system with subsequent accumulation of toxic levels of acetylcholine.
Organophosphorus pesticides in common use are rapidly biotransformed and excreted, and sub-acute or chronic poisoning by virtue of accumulation of the compounds in the body does not occur.
Organophophorus insecticides: a general introduction (EHC 63, 1986) (14345 words)
Methods for assessing absorption and effects of organophosphorus insecticides 7.1.1.1 Analysis of urine as a means of monitoring exposed populations 7.1.1.2 Biochemical methods for the measurement of effects 7.1.1.3 Electrophysiological methods for the study of effects 7.1.2.
Further studies are necessary on the occurrence of organophosphorus insecticides in the different food chains (bioaccumulation) and in the food and drinking-water of man (market basket or total-diet studies), in order to estimate the daily exposure of the population.
Most organophosphorus pesticides are degraded quickly by the metabolic reactions listed in section 4.3, and the elimination of the products, mostly in the urine with lesser amounts in faeces and expired air, is not delayed, so that rates of excretion usually reach a peak within 2 days and decline quite rapidly.
  More results at FactBites »


 

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